9-(2-O-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-6-chloro-2-iodopurine | 879398-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-(2-O-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-6-chloro-2-iodopurine
• CAS: 879398-49-9
• 化学式: C₁₃H₁₂ClIN₈O₄
• 分子量: 506.647
• InChiKey: GBXPYPSIUIOLTJ-ADVRJHOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  156.99
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  9-(2-O-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-6-chloro-2-iodopurine 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 氨 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of hypermodified adenosine derivatives as selective adenosine A3 receptor ligands

  摘要：

  We investigated the A(3)AR affinity and selectivity of a series of 2-substituted 3'-azido and 3'-amino adenosine derivatives as well as some 5-uronamide derivatives thereof. All compounds showed high A3AR selectivity. While the 3'-azides appeared to be A3AR antagonists with moderate A3AR affinity, their 3'-amino congeners exhibit significantly improved A3AR affinity and behave as partial agonists. For both the 3'-azides and the 3'-amines, the 5'-methylcarbamoyl modification improved the overall affinity. Introduction of a 2-phenylethynyl substituent provided high affinity for the A3AR. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.062
• 作为产物：
  描述：

  9-(2-O-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-2-amino-6-chloropurine 在 copper(l) iodide 二碘甲烷 、 碘 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以79%的产率得到9-(2-O-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-6-chloro-2-iodopurine
  参考文献：
  名称：

  Synthesis of hypermodified adenosine derivatives as selective adenosine A3 receptor ligands

  摘要：

  We investigated the A(3)AR affinity and selectivity of a series of 2-substituted 3'-azido and 3'-amino adenosine derivatives as well as some 5-uronamide derivatives thereof. All compounds showed high A3AR selectivity. While the 3'-azides appeared to be A3AR antagonists with moderate A3AR affinity, their 3'-amino congeners exhibit significantly improved A3AR affinity and behave as partial agonists. For both the 3'-azides and the 3'-amines, the 5'-methylcarbamoyl modification improved the overall affinity. Introduction of a 2-phenylethynyl substituent provided high affinity for the A3AR. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.062